


Tai's Little Girly Nightmare

by J13579



Category: Digimon Adventure
Genre: Crossdressing, Dreams and Nightmares, Forced Crossdressing, Gen, Nightmares
Language: English
Status: Completed
Published: 2019-02-11
Updated: 2019-02-11
Packaged: 2019-10-26 04:43:57
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,043
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17739236
Author URL: https://archiveofourown.org/users/J13579/pseuds/J13579
Summary: A mere loss of a bet quickly turns into a nightmare for Tai.





	Tai's Little Girly Nightmare

“But Mom,” Tai pleaded.

“No buts, Tai,” his mother scolded him. “If you didn’t want to do this, then you shouldn’t have made that stupid bet with your sister in the first place. Now put on the clothes your sister picked for you.

Admitting defeat, Tai stared at the clothes laid out for him. It was one of Kari’s dresses. It was a frilly yellow party dress with puffy sleeves, a sash tied into a bow on the back and a built-in petticoat. Right next to the dress was a pair of white tights and yellow Mary Janes. The frilly yellow panties completed the outfit. 

“This is ridiculous,” Tai slowly took his clothes off before picking up the panties. “They’ll never fit me.” He slipped his feet through the holes and pulled them up. So much tighter than his usual boxers. He quickly repeated the process for the tights before slipping on the yellow Mary Janes. on the yellow dress. 

Once he was fully dressed, Tai left the room.

“My god,” Yuuko gasped. “It actually fits you.”

“Wait, what?” Tai turned to the mirror. Much to his shock, his mom was right. His little sister’s clothes did fit him. A bit too well, almost like they morphed to fit him. 

“See, Mom,” Kari pointed to Tai. “I told you that they looked good on him. Maybe we should get him some cute dresses too.”

Tai rolled his eyes, “Yeah, right.”

“Oh,” Kari took out a hairbrush and some yellow hair ribbons. “Let me do your hair.” She ran up to Tai and in less than a minute, his hair was up in pigtails, tied in big yellow bows.

“My hair.” Tai wanted to cry. He loved how he did his hair and now it was tied up in bows like a five year old. 

“Oh Tai,” Kari giggled. “You look so cute with your hair like that. Well Mom, think we should get Tai some cute dresses of his own?”

Yuuko briefly paused in thought for just a brief moment before saying, “Well Tai, your clothes are rather old and ripped.”

“What are you saying?” Tai asked. He could feel dread going up his entire body. 

“I’m saying,” Yuuko grabbed his hand. “We’re going shopping. Come on Kari.”

Before Tai knew it, he was at the mall with his mom and sister picking out dresses for him.

“Hey, Mom,” Kari held up two dresses. “Should we get Tai this fluffy white dress with all of these petticoats or this pink one with hearts and rainbows all over it.

“How about we let Tai pick?” Yuuko turned to her son. “Which dress do you want, sweetie?”

Tai just turned away in a huff. “I’m not picking.”

“We’ll take both, then.”

“Tai,” Kari whined. “You’ll look so cute in these dresses. Why don’t you try them on?”

“Because I look stupid like this.”

“No you won’t,” Kari replied. “You look so cute and adorable with your new look.

“But if my friends see me like this, they will never let me play soccer with them again,” Tai begged. “I’ll be the laughingstock of the whole school.”

His response was a bunch of snickering from both Kari and their mom. 

“Tai, we would never allow you to play soccer in your new clothes. You’ll ruin them playing those rough sports with your friends,” Yuuko explained. “I think it’s time you take up some new hobbies more in line with your sister’s. I’m pulling you off the team.” 

“Yeah,” Kari added. “But don’t feel bad. I have a few friends that can help you find some new activities to play like hopscotch and dress-up. Now let’s get some anklets with that white dress. I think it’ll look super cute on you.” 

By the time they got back home, Tai had about twenty dresses with each of them being as cute and childish as possible. All of them with their own shoes, socks and cute little accessories. 

Once they got back, Kari and Yuuko immediately went over to Tai’s room with a box of garbage bags. Each and every article of male clothing was immediately thrown into those garbage bags and the bags in turn were thrown into the dumpster outside. 

“By the way, I called all of our friends,” Kari said. “They’re coming over.”

“You did what?” Tai gasped.

“Well, they are going to find out sooner or later,” Tai’s sister explained. “So, I told them everything and they’re just dying to see your new look.”

“W-what?” Tai stammered. He could hear all too familiar footsteps approaching him. A quick turn and there they are; Matt, Joe, Izzy, Sora, Mimi and T.K. All of them are there while Tai was dressed in the most childish attire he bet they have ever seen. His cheeks grew increasingly red as they stood there in silence. 

After a brief moment, the other digidestined began laughing at Tai’s predicament. To make matters worse, Sora and Mimi rushed up to him. 

“Awww,” Mimi cooed. “You look so cute, Tai. I want to pinch those little cheeks.” Before Tai could respond, Mimi grabbed his hand and held it tight. “We got to show off your new look to your teammates.”

“Come on, Tai,” Sora took Tai’s other hand in an equally tight grip. “We need to explain to your coach why your mom won’t let you play soccer anymore.” And so the two girls began to make their way outside, dragging Tai behind them.

“Noooooooo!” Tai yelled. He tried to fight back; he tried to tug his hands out of their grips, digging his soles of his Mary Janes into the ground as hard as he can. But Sora and Mimi were too strong for him. Matt opened the front door, revealing a bright flash of light. 

And as quickly as the flash came, Tai’s eyes opened. He looked around his room, a quick glance at his closet revealed his own clothes, no dresses in sight. He was still in his pajamas. Tai breathe a sigh of relief. “Just a bad dream.”

“Hey Tai,” the boy turned to see Kari standing by the doorway. “Are you okay?

“It’s nothing. I just had a dumb nightmare.”

“Really?” Kari replied. “What was it about?”

**Author's Note:**

> Hey guys, I know it's been a while, but I'm currently busy with college so I decided to give you something short and sweet while I'm working on other stuff in my spare time.


End file.
